Manufacture of vat dyestuffs.



UNITED STATES PATENT OFFICE.

EDWARD WRAY, OF BIEBRICH-ON-THE-RHINE, GERMANY, ASSIGNOR TO THE FIRM OF KALLE AND COMPANY, AKTIENGESELLSCHAFT, OF BIEBRICH-ON-THE-RHINE,

Patented Aug. 18, 1914.

GERMANY. MANUFACTURE OF VAT DYESTUFFS.

1,108,057. 4 Specification. of Letters Patent.

No Drawing. Application filed October 29, 1913. Serial No. 798,106.

To all whom it may concern: Be it known that I, EDWARD WRAY, chemist, and subject of the King of England, re-

siding at 82 Rathausstrasse, Biebrich-on-- vat dyestufis are obtained. Now, I have found that also valuableindigoid coloring matters can be obtained by combining the 2- derivatives of the 2.3-diketodihydro-l-thionaphthene, their homologues or analogues with the above named pheno-oxy-naphthocarbazoles, their substitution products, ho-

, mologues or analogues.

The products of the present invention have a constitution represented graphically where R is the aromatic residue of the thionaphthene which may or may not be substituted and R is the radical of the na htho-carbazole.

xample: 23 parts of 2.1-pheno-5-oxynaphtho-carbazole of the following formula:

pheno-oxywhereupon 30 parts of 2-dibromo-3-ketodihydro-l-thionaphthene are gradually added in small portions. The dyestufl separates at once, it is filtered oil in a hot condition and washed with some glacial acetic acid and alcohol. It has the following graphi= cally represented constitution:

In a dry state it forms a bronze-like redviolet powder soluble in ulfuric acid with a green color. When reduced it forms a yellowish vat from which cotton is dyed very fast reddish-violet shades becoming redder on soaping.

The indigoid coloring matters thus produced may be treated with halogen and thus converted into halogenated derivatives. For instance, the above described condensationproduct obtained from 2-dibromo-3-ketodihydro-l-thionaphthene and 2.1-pheno-oxynaphtho-carbazole, when brominated in nitrobenzene, furnishes a halogenated derivative in the form, of a blue-violet powder which is soluble in sulfuric acid with a bluish-green color. It yields on treatment with a solution of hydrosulfite and alkali a yellow vat from which cotton is dyed blueviolet shades becoming redder on soaping.

I claim:

1. Process for producing vat dyestu'fi's which consists in condensing the 2-derivatives of the 2.3-diketodihydro-l-thionaphthene with pheno-oxy-naphtho-carbazole.

2. Process for producing vat dyestufi's which consists in condensing 2-dibromo-3- ketodihydro 1 thionaphthene with 2 1 pheno-5-oxy naphtho-carbozole.

3. As new products the indigoid coloring matters obtainable by condensing the 2derivetives of the 2.3 diketoclihydrw1--tliionephthenes with pheno-oXy-naphtho-cerhwzoles having the following graphically representerl constitution where R. IS the aromatic nucleus of the thionaplithene end B the radical of the phenooXy napththo carbazole, forming in dry stateretl-violet powders, insoluble in Water,

I scarcely soluble in alcohol, soluble in hot nifirobenzene and quinolin, also soluble in sulfuric acid with a green color, being reduced on treatment with alkaliend hydrosulfite to a yellow vet from. which cotton is dyeii Very fast red-violet shades.

4-. As a new product the indigoicl coloring matter from 2-(libromo-3ketoclihydro l- 'thionaphthene and 2.1-pheno-5-oxy-naphf'aho-cerhazole of the following ,constitutioni- I 7 L 5 4 I. Y i I 

